Isochroman musk compounds and organoleptic uses thereof

ABSTRACT

Processes and compositions are described for the use in foodstuff flavor and aroma and perfume and perfumed article aroma augmenting, modifying, altering, and enhancing compositions and as foodstuff, chewing gum, toothpaste, medicinal product, perfume and perfumed article aroma imparting materials of indane alkanols and tricyclic isochromans defined according to the generic structure: ##STR1## wherein R 1  is hydrogen or methyl; R 2 , R 3 , R 4  and R 5  represent hydrogen, methyl or isopropyl; the dashed line represents a carbon-carbon single bond or no bond; X represents --CH 2  --, CH 3  or hydrogen; with the proviso (i) that R 2  and R 3  represent methyl when R 4  is hydrogen and R 5  is isopropyl and R 4  and R 5  represent methyl when R 2  is hydrogen and R 3  is isopropyl; and the dashed line represents a carbon-carbon single bond when X is --CH 2  -- and the dashed line represents no bond when X is hydrogen or CH 3 . 
     Addition of said indane alkanols and tricyclic isochromans or mixtures thereof is indicated to produce: 
     (a) In food flavorings, a sweet, musky aroma and taste; and 
     (b) In perfumes and perfumed articles and colognes, a sweet, musk aroma.

This application is a divisional of application for United StatesLetters Pat. Ser. No. 63,374 filed on Aug. 3, 1979, now U.S. Pat. No.4,250,200 issued on Feb. 10, 1981.

BACKGROUND OF THE INVENTION

The present invention relates to indane alkanols and tricyclicisochromans and mixtures containing same as well as organoleptic usesthereof to alter, modify, augment, enhance or impart flavors and/oraromas in (or to) consumable materials.

There has been considerable work performed relating to substances whichcan be used to impart (or alter, modify or enhance) flavors andfragrances to (or in) various consumable materials. These substances areused to diminish the use of natural materials, some of which may be inshort supply and to provide more uniform properties in the finishedproduct. Sweet and musky aroma characteristics and sweet and muskyflavor characteristics are particularly desirable for many uses infoodstuff flavors, particularly pear, apricot and peach flavors. Muskyaromas are desirable in several types of perfume compositions and foruse in perfumed articles.

The production of isochromans has been shown in the prior art andcertain novel isochromans have recently been disclosed with anoutstanding musk fragrance. Such isochromans especially adapted forperfumery by virtue of their fragrance properties have been disclosed inHeeringa and Beets, U.S. Pat. No. 3,360,530 issued on Dec. 26, 1967.

A number of routes have been shown to be available for the production ofisochromans, such as those set forth in U.S. Pat. No. 3,360,530 and oneof the most straight forward of these routes is treatment of a FriedelCrafts reactant with an alkylene oxide under Friedel Crafts conditionsto form an aryl alkanol. The aryl alkanol is then isolated andthereafter reacted with formaldehyde to cyclialkylate the alcohol.

In addition, several other references set forth processes for theproduction of isochromans such as U.S. Pat. No. 3,532,719 and U.S. Pat.No. 3,910,964 as well as U.S. Pat. No. 3,978,090.

The aforementioned references set forth production of compounds havingthe structures: ##STR2## using as a precursor pentamethyl indane havingthe structure: ##STR3## None of these references implies production ofcompounds having any of the structures: ##STR4## using as a precursorthe tetraalkyl indane having the structure: ##STR5##

U.S. Pat. No. 3,400,159 issued on Sept. 3, 1968 entitled "NovelMusk-Like Substituted Acenaphthene and Process" discloses broadly atcolumn 3, lines 42-61 that compounds having the formula: ##STR6## may beemployed in "the same manner as other musk-like compounds alone or inadmixture with other ingredients". It is further disclosed that suchcompounds may be used in perfumes, lotions, powders, soaps and the likecontaining one or more odorants or flavoring substances. The use of suchcompounds in foodstuffs, however, is not disclosed per se. Indeed, thestatement that such compounds can be used "with other flavoringsubstances" is not preceded by an antecedent statement that there isutility of such compounds in flavoring or in augmenting, or enhancingthe flavor of foodstuffs.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 represents the GLC profile for the reaction product of Example Icontaining compounds having the structures: ##STR7##

FIG. 2 is the NMR spectrum for compounds having the structures: ##STR8##produced according to Example I.

FIG. 3 is the CMR spectrum for compounds having the structures: ##STR9##produced according to Example I.

FIG. 4 is the infrared spectrum for compounds having the structures:##STR10## produced according to Example I.

FIG. 5 is the GLC profile for compounds having the structures: ##STR11##produced according to Example II.

FIG. 6 is the NMR spectrum for compounds having the structures:##STR12## produced according to Example II.

FIG. 7 is the infrared spectrum for compounds having the structures:##STR13## produced according to Example II.

FIG. 8 is the GLC profile for compounds having the structures: ##STR14##produced according to Example III.

FIG. 9 is the NMR spectrum for compounds having the structures:##STR15## produced according to Example III.

FIG. 10 is the infrared spectrum for compounds having the structures:##STR16## produced according to Example III.

FIG. 11 is the GLC profile for compounds having the structures:##STR17## produced according to Example IV.

FIG. 12 is the NMR spectrum for compounds having the structures:##STR18## produced according to Example IV.

FIG. 13 is the infrared spectrum for compounds having the structures:##STR19## produced according to Example IV.

FIG. 14 is the GLC profile for compounds having the structures:##STR20## produced according to Example V.

FIG. 15 is the NMR spectrum for compounds having the structures:##STR21## produced according to Example V.

FIG. 16 is the infrared spectrum for compounds having the structures:##STR22## produced according to Example V.

THE INVENTION

It has now been discovered that novel solid and liquid foodstuff,chewing gum, medicinal products, and flavoring compositions thereforhaving pear, peach or apricot flavors with sweet, musky aromacharacteristics and sweet and musky flavor characteristics and novelperfume compositions, colognes and perfumed articles having sweet, muskyaromas may be provided by indane alkanols and tricyclic isochromanshaving the generic structure: ##STR23## wherein R₁ is hydrogen ormethyl; R₂, R₃, R₄ and R₅ represent hydrogen, ethyl or isopropyl; thedashed line represents a carbon-carbon single bond or no bond; Xrepresents--CH₂ --, CH₃ or hydrogen; with the proviso (i) that R₂ and R₃represent methyl when R₄ is hydrogen and R₅ is isopropyl and R₄ and R₅represent methyl when R₂ is hydrogen and R₃ is isopropyl; and the dashedline represents a carbon-carbon single bond when X is --CH₂ --and thedashed line represents no bond when X is hydrogen or CH₃ and morespecifically compounds having the structures: ##STR24## wherein R₁, R₂,R₃, R₄ and R₅ are defined as above.

The indane alkanols and tricyclic isochromans of our invention havingthe generic structure: ##STR25## may be prepared according to processesillustrated by the following reaction schemes: ##STR26## and the reactonof the tetraalkyl indane with the alkylene oxide, the reactiontemperature may vary from 0° C. to 40° C. with the mole ratio ofhydrocarbon starting material: epoxide being from 1:1 up to 5:1 with aratio of 3:1 being optimum. The ratio of catalyst (Lewis Acid, such asaluminum trichloride):epoxide should be about 1:1. The reaction can becarried out in the present of a co-solvent, such as carbontetrachloride, chloroform, dichloro benzene, acetone, hexane, orisooctane. In the second step, the cyclization of the indane alkanol toform the tricyclic isochroman, the reaction temperature should be in therange of 80° C. up to 150° C. with a mole ratio of starting indanealkanol: formaldehyde source being from 1:1 up to 3:1 with a ratio of1.5:1 being optimum. The mole ratio of indane alkanol:formaldehydesource should be from 1:1 up to 3:1 with 2:1 being optimum. The moleratio of paratoluene sulfonic acid to indane alkanol should be from 0.1up to 0.4:1.

The process for producing the tricyclic isochroman may be in accordancewith the processes set forth in Examples I and II of U.S. Pat. No.3,910,964 issued on Oct. 7, 1975.

The indane alkanols and tricyclic isochromans of our invention arecapable of supplying and/or potentiating certain flavor and aroma notesusually lacking in many food flavors, particularly peach flavors,apricot flavors and pear flavors. Furthermore, the indane alkanols andtricyclic isochromans of our invention are capable of supplying certainfragrance notes usually lacking in many perfume materials, for example,musk fragrances.

The indane alkanols and tricyclic isochromans of our invention have thefollowing organoleptic properties:

                  TABLE I                                                         ______________________________________                                        FRAGANCE PROPERTIES                                                                             ORGANOLEPTIC                                                COMPOUND MIXTURE  PROPERTIES                                                  ______________________________________                                        Mixture of isochromans                                                                          A sweet, musky aroma.                                       having the structures:                                                         ##STR27##                                                                    and                                                                            ##STR28##                                                                    Mixture of compounds                                                                            A sweet, musky aroma with                                   having the structures:                                                                          delicate animal musk nuances.                                ##STR29##                                                                    and                                                                            ##STR30##                                                                    Mixture of compounds                                                                            A coarse, chemical musk note.                               having the structures:                                                         ##STR31##                                                                    and                                                                            ##STR32##                                                                

                  TABLE II                                                        ______________________________________                                        FLAVOR PROPERTIES                                                                               ORGANOLEPTIC                                                COMPOUND MIXTURE  PROPERTIES                                                  ______________________________________                                        Mixture of compounds                                                                            A musky, animal aroma                                       having the structures:                                                                          character with a sweet,                                                       musky flavor character                                                        at 1 ppm.                                                    ##STR33##                                                                    and                                                                            ##STR34##                                                                    Mixture of compounds                                                                            A sweet, musky aroma and                                    having the structures:                                                                          flavor characteristic at                                                      0.002 ppm.                                                   ##STR35##                                                                    and                                                                            ##STR36##                                                                

When the indane alkanols and tricyclic isochromans of our invention areused as food flavor adjuvants, the nature of the co-ingredients includedwith said indane alkanols and tricyclic isochromans in formulating theproduct composition will serve to alter the organoleptic characteristicsof the ultimate foodstuff treated therewith.

As used herein in regard to flavors, the terms "alter" and "modify" intheir various forms means "supplying or imparting flavor character ornote to otherwise bland, relatively tasteless substances or augmentingthe existing flavor characteristic where a natural flavor or syntheticflavor or mixture of natural synthetic flavors is deficient in someregard, or supplementing the existing flavor impression to modify itsquality, character or taste".

As used herein, the term "enhance" is intended to means theintensification (without effecting a change in kind of quality or aromaor taste) of one or more taste and/or aroma nuances present in theorganoleptic impression of a consumable material, e.g., foodstuff,tobacco, chewing gum, medicinal product, perfume composition or perfumedarticle.

As used herein, the term"foodstuff" includes both solid and liquidingestible materials which usually do, but need not, have nutritionalvalue. Thus, foodstuffs include soups, convenience foods, beverages,dairy products, candies, vegetables, cereals, soft drinks, snacks andthe like.

As used herein, the term "chewing gum" is intended to mean a compositionwhich comprises a substantially water-insoluble, chewable plastic gumbase such as chicle, or substitutes therefor, including jelutung,guttakay rubber and/or certain comestible natural or synthetic resins orwaxes. Incorporated within the gum base, in admixture therewith may beplasticizers or softening agents, e.g., glycerine; and a flavoringcomposition which incorporates the indane alkanols and tricyclicisochromans of our invention, and, in addition, sweetening agents whichmay be sugars, including surcrose or dextrose and/or arrificialsweeteners including dipeptides, cyclamates and saccharin. Otheroptional ingredients may also be present.

The term "medicinal product" includes both solids and liquids which areingestible, non-toxic materials having medicinal value such as coughsyrups, cough drops, toothpast, aspirin and chewable medicinal tabletsas further exemplified herein.

Substances suitable for use herein as co-ingredients or flavoringadjuvants are well known in the art for such use being extensivelydescribed in the relevant literature. Such material is required to be"ingestibly" acceptable and thus non-toxic or otherwise non-deleterious.Particularly critical is the additional requirement that such materialbe organoleptically compatible with the indane alkanols and tricyclicisochromans encompassed within the scope of our invention. Also criticalis the additional requirement that such material be nonreactive (withinthe range of storage conditions and room temperature use conditions)with indane alkanols and tricyclic isochromans.

Accordingly, such materials which may in general be characterized asflavoring adjuvants or vehicles comprise broadly stabilizers,thickeners, surface active agents, conditioners, other flavorants andflavor intensifiers.

Stabilizer compounds include preservatives, e.g., sodium chloride;antioxidants, e.g., calcium and sodium ascorbate, ascorbic acid,butylated hydroxyanisole (mixture of 2- and3-tertiary-butyl-4-hydroxyanisole), butylated hydroxy toluene,(2,6-di-tertiary-butyl-4-methyl phenol), propyl gallate and the like andsequestrants, e.g., citric acid.

Thickener compounds include carriers, binders, protective colloids,suspending agents, emulsifiers, and the like, e.g., agaragar,carrageenan; cellulose and cellulose derivatives such as carboxymethylcellulose and methyl cellulose; natural and synthetic gums such as gumarabic, gum tragacanth; gelatin, proteinaceous materials; lipids,carbohydrates, starches, pectins, and emulsifiers, e.g., mono- anddiglycerides of fatty acids, skim silk powder, hexoses, pentoses,disaccharides, e.g., sucrose, corn syrup and the like.

Surface active agents include emulsifying agents e.g., fatty acids suchas capric acid, caprylic acid, palmitic acid, myristic acid and thelike, mono- and diglycerides of fatty acids, lecithin, defoaming andflavor-dispersing agents, such as sorbitan monostearate, potassiumstearate, hydrogenated tallow alcohol and the like.

Conditioners include compounds such as bleaching and maturing agents,e.g., benzoyl peroxide, calcium peroxide, hydrogen peroxide and thelike; starch modifiers such as peracetic acid, sodium chlorite, sodiumhypochlorite, propylene oxide, succinic anhydride and the like, buffersand neutralizing agents, e.g., sodium acetate, ammonium bicarbonate,ammonium phosphate, citric acid, lactic acid, vinegar and the like;colorants, e.g., carminic acid, cochineal, turmeric and curcuma and thelike, firming agents such as aluminum sodium sulfate, calcium chlorideand calcium gluconate; texturizers, anti-caking agents, e.g., aliminumcalcium sulfate and tribasic calcium phosphate; enzymes, yeast foods,e.g., calcium lactate and calcium sulfate; nutrient supplements, e.g.,iron salts such as ferric phosphate, ferrous gluconate and the like,riboflavin, vitamins, zinc sources such as zinc chlroide, zinc sulfateand the like.

Other flavorants and flavor intensifiers include organic acids, e.g.,acetic acid, formic acid, 2-hexenoic acid, benzoic acid, n-butyric acid,caproic acid, caprylic acid, cinnamic acid, isobutyric acid, isovalericacid, alpha-methy-butyric acid, propionic acid, valeric acid, cis andtrans 2-methyl-2-pentenoic acid, and cis and trans 2-methyl-3-pentenoicacid; ketones and aldehydes, e.g., acetaldehyde, acetophenone, acetone,acetyl methyl carbinol, acrolein, n-butanal, crotonal, diacetyl, beta,beta-dimethyl-acrolein, n-hexanal, 2-hexenal, cis-3-hexenal, 2-heptenal,4-(p-hydroxyphenyl)-2-butanone, alpha-ionone, beta-ionone,methyl-3-butanone, 2-pentanone, 2-pentenal and propanal; alcohols suchas 1-butanol, benzyl alcohol, 1-borneol, trans -3-buten-1-ol, ethanol,geraniol, 1-hexanol, 2-heptenol-1, trans-3-hexenol-1, cis-3-hexen-1-ol,3methyl-3-buten-1-ol, 1-penten-2-ol, 1-penten-3-ol,p-hydroxyhenyl-2-ethanol, isoamyl alcohol, isofenchyl alcohol,phenyl-2-ethanol, alpha-terpineol, cis-terpineol hydrate; esters, suchas butyl acetate, ethyl acetate, ethyl acetoacetate, ethyl benzoate,ethyl butyrate, ethyl caproate, ethyl cinnamate, ethyl crotonate, ethylformate, ethyl isobutyrate, ethyl isovalerate, ethylalpha-methylbutyrate, ethyl propionate, ethyl salicylate, trans-2-hexenyl acetate, hexyl acetate, 2-hexenyl butyrate, n-hexyl butyrate,isoamyl acetate, isopropyl butyrate, methyl actate, methyl-n-butyrate,methyl caproate, methyl isobutyrate, alpha-methyl-n-butyrate, n-propylacetate, n-amyl acetate, n-amyl-n- butyrate, benzyl salicylate, dimethylanthranilate, ethyl methylphenylglycidate, ethyl succinate, isobutylcinnamate, and terpenyl acetate; lactones, such as delta-decalactone,delta-undecalactone, delta-nonyl-lactone, gamma-undecalactone,gamma-dodecalactone and gamma nonyl-lactone as well as "peach" lactones;essential oils, such as jasmine absolute, rose absolute, orris absolute,lemon essential oil, Bulgarian rose, yara yara, natural raspberry oiland vanila; sulfides, e.g., methyl sulfide and other materials such asmaltol, acetoin, acetals (e.g., 1,1-diethoxyethane, 1,1-dimethoxyethaneand dimethoxymethane) and 2- and 3- cyclotetradecene-1-ones having oneof the structures: ##STR37## described in application for United StatesLetters Patent, Ser. No. 973,093 filed on Dec. 26, 1978.

The specific flavoring adjuvant selected for use may be either solid orliquid depending upon the desired physical form of the ultimate product,i.e., foodstuff whether simulated or natural, and should, in any event,be capable of providing an environment in which the indane alkanols andtricyclic isochromans can be dispersed or admixed to provide ahomogeneous medium. In addition, selection of one or more flavoringadjuvants, as well as the quantities thereof will depend upon theprecise organoleptic character desired in the finished product. Thus, inthe case of flavoring compositions, ingredient selection will vary inaccordance with the foodstuff to which the flavor and aroma are to beimparted. In contradistinction, in the preparation of solid products,e.g., simulated foodstuffs, ingredients capable of providing normallysolid compositions should be selected such as various cellulosederivatives.

As will be appreciated by those skilled in the art, the amount of indanealkanols and tricyclic isochromans employed in a particular instance canvary over a relatively wide range whereby specific desired organolepticeffects (having particular reference to the nature of the product) areachieved. Thus, correspondingly greater amounts would necessary in thoseinstances wherein the ultimate food composition to be flavored isrelatively bland to the taste, whereas relatively minor quantitites maysuffice for purposes of enhancing the composition merely deficient innatural flavor or aroma. The primary requirement is that the amountselected be effective, i.e., sufficient to alter, modify, or enhance theorganoleptic characteristics of the parent composition, whetherfoodstuff per se or flavoring composition.

The use of insufficient quantities of indane alkanols and tricyclicisochromans will, of course, substantially vitiate any possibility ofobtaining the desired results while excess quantities prove needlesslycostly and in extreme cases, may disrupt the flavor-aroma balance, thusproving self-defeating. Accordingly, the terminology "effective amount"and "sufficient amount" is to be accorded a significance in the contextof the present invention consistent with the obtention of desiredflavoring effects.

Thus, and with respect to ultimate food compositions, it has been foundthat quantities of indane alkanols and tricyclic isochromans rangingfrom a small but effective amount, e.g., 0.0001 parts per million up toabout 50 parts per million by weight based on total composition aresuitable. Concentrations in excess of the maximum quantity stated arenot normally recommended, since they fail to provide commensurateenhancement or augmentation of organoleptic properties. In thoseinstances wherein the indane alkanols and tricyclic isochromans areadded to the foodstuff as an integral component of a flavoringcomposition, it is, of course, essential that the total quantity offlavoring compositon employed be sufficient to yield an effectiveconcentration (of indane alkanols and tricyclic isochromans) in thefoodstuff product.

Food flavoring compositions prepared in accordance with the presentinvention preferably contain the indane alkanols and tricyclicisochromans in concentrations ranging from about 0.01% up to about 15%by weight based on the total weight of the said flavoring composition.

The compositions described herein can be prepared according toconventional techniques well known as typified by cake batters and fruitdrinks and can be formulated by merely admixing the involved ingredientswithin the proportions stated in a suitable blender to obtain thedesired consistency, homogeneity of dispersion, etc. Alternatively,flavoring compositions in the form of particulate solids can beconveniently prepared by mixing the indane alkanols and tricyclicisochromans with, for example, gum arabic, gum tragacanth, carrageenanand the like, and thereafter spray-drying the resultant mixture wherebyto obtain the particulate solid product. Pre-prepared flavor mixes inpowder form, e.g., a fruit-flavored powder mix are obtained by mixingthe dried solid components, e.g., starch sugar and the like and indanealkanols and/or tricyclic isochromans in a dry blender until therequisite degree of uniformity is achieved.

It is presently preferred to combine with indane alkanols and tricyclicisochromans, the following adjuvants:

p-Hydroxybenyl acetone;

Geranoil;

Acetaldehyde;

Maltol;

Ethyl methyl phenyl glycidate;

Benzyl acetate;

Dimethyl sulfide;

Vanillin;

Methyl cinnamate;

Ethyl pelargonate;

Methyl anthranilate;

Isoamyl acetate;

Isobutyl acetate;

Alpha ionone;

β-Damascone;

β-Damascenone;

Ethyl butyrate;

Acetic acid;

n-Hexyl acetate;

n-Hexyl isobutyrate;

Trans-2-hexenal;

Linalyl isobutyrate;

n-Hexyl-2-methyl-n-butyrate;

Gamma-undecalactone;

Gamma-nonalactone;

Gamma-decalactone;

Delta undecalactone;

Delta dodecalactone;

Delta nonyl lactone;

"Peach" lactone;

Naphthyl ethyl ether;

Diacetyl;

Apple Fusel Oil;

Sauge Sclaree;

Coriander Oil;

Ethyl acetate;

Anethole;

Isoamyl-n-butyrate;

Ethyl-2-methyl-cis-3-pentenoate;

Cis-3-hexenol-1;

2-Methyl-cis-3-pentenoic acid;

2-Methyl-2-pentenoic acid;

Elemecine (4-allyl-1,2,6-trimethoxy benzene);

Isoelemecine (4-propenyl-1,2,6-trimethoxy benzene);

2-(4-hydroxy-4-methylpentyl) norbornadiene prepared according to U.S.Pat. No. 3,886,289; and

2- and 3-Cyclotetradecen-1-ones having the structures: ##STR38##described according to Application for United States Letters Patent,Ser. No. 973,093 filed on Dec. 26, 1978

The indane alkanols and tricyclic isochromans and one or more auxiliarlyperfume ingredients including, for example, alcohols other than theindance alkanols of our invention, aldehydes, nitriles, esters, cyclicesters, ketones, ethers other than the tricyclic isochromans of ourinvention, natural essential oils and synthetic essential oils may beadmixed so that the combined odors of the individual components producea pleasant and desired fragrance, particularly and preferably, in muskand "animal-like" fragrances. Such perfume compositions usually contain(a) the main note or the "bouquet" or foundation stone of thecomposition; (b) modifiers which round off and accompany the main note;(c) fixatives which include odorous substances which lend a particularnote to the perfume throughout all stages of evaporation and substanceswhich retard evaporation; and (d) topnotes which are usually low boilingfresh smelling materials.

In perfurme compositions, it is the individual components whichcontribute to its particular olfactory characteristics, but the over-alleffect of the perfume composition will be the sum of the effects of eachof the ingredients. Thus, the indane alkanols and tricyclic isochromanscan be used to alter the aroma characteristics of a perfume composition,for example, by utilizing or moderating the olfactory reactioncontributed by at least one other ingredient in the composition.

The amount of indance alkanols and tricyclic isochromans of ourinvention which will be effective in perfume compositions depends onmany factors including the other ingredients, their amounts and theeffects which are desired. It has been found that perfume compositionscontaining as little as 0.01% of indane alkanols and tricylicisochromans and even less (e.g., 0.005%) can be used to impart a sweet,musk aroma for soaps, anionic, cationic, and nonionic detergents, fabricsoftener articles and compositions of matter, cosmetics or otherproducts. The amount employed can range up to 10% of the fragrancecomponents and can range up to 0.5% of the weight of the perfumedarticle and will depend upon considerations of cost, nature of the endproduct, the effect desired on the finished product and the particularfragrance sought.

The indane alkanols and tricyclic isochromans are useful, taken alone orin perfume compositions as olfactory components in anionic, cationic andnonionic detergents, soaps, fabric softener compositions, fabricsoftener articles for use in clothes dryer (e.g., "BOUNCE"®, aregistered trademark of the Procter & Gamble Company of Cincinnati,Ohio), space odorants and deodorants, perfumes, colognes, toilet water,bath preparations, such as lacquers, brilliantines, creams, deodorants,hand lotions and sun screens; powders, such as talcs, dusting powders,face powders and the like. When used as an olfactory component inperfume compositions or perfumed articles, such as anionic, cationic andnonionic detergents and in fabric softener compositions and fabricsoftener articles (e.g., for use in clothing dryers) as little as 0.05%of the indance alkanols and tricyclic isochromans of our invention willsuffice to impart an intense sweet, musk fragrance. Generally, no morethan 5% of the indane alkanols and tricyclic isochromans based on theultimate end product is required in the perfume composition or in theperfumed article.

In addition, the perfume composition or fragrance composition of ourinvention can contain a vehicle or carrier for the indane alkanols andtricylcic isochromans. The vehicle can be a liquid such as a non-toxicalcohol, a non-toxic glycol, or the like. The carrier can also be anabsorbent solid, such as a gum (e.g., gum arabic) or components forencapsulating the composition (such as gelatin) as by means ofcoacervation.

It will thus be apparent that the indane alkanols and tricyclicisochromans of our invention can be utilized to alter the sensoryproperties, particularly organoleptic properties, such as flavors and/orfragrances of a wide variety of consumable materials.

The following examples are illustrative and the invention is to beconsidered restricted thereto only as indicated in the appended claims.All parts and percentages given herein are by weight unless otherwisespecified.

EXAMPLE I Preparation of 3-Isopropyl-β,1,1,2-Tetramethyl-5-Indanethanoland 1-Isopropyl-β,2,3,3-Tetramethyl-5-Indanethanol ##STR39##

A well-stirred mixture of 1,1,2-trimethyl-3-isopropylindane (600 grams,isooctane (240 grams), and aluminum chloride (294 grams) is cooled to-10° C. To this stirred slurry is added a solution of1,1,2-trimethyl-3-isopropylindane (410 grams), isocotane (240 grams),and propylene oxide via a subsurface addition inlet. The reaction massis kept at -10° C. to -5° C. The addition is accomplished in threehours. After the addition, the mass is stirred at -10° C. for tenminutes and then poured into 4 liters of stirred ice water. Afterstirring 10 minutes, the bottom layer is discarded. The organic layer iswashed with water, then aqueous sodium bicarbonate. Distillation througha short column affords 840 grams of recovered1,1,2-trimethyl-3-isopropylindane and 225 grams of crude product.Fractional distillation through a 1"×12" Goodloe® packed column affordsgood-odored product consisting of a mixture of3-isopropyl-β,1,1,2-tetramethyl-5-indanethanol and1-isopropyl-β,2,3,3-tetramethyl-5-indanethanol(b.p. 142° C. at 1.2 mmHg. pressure).

FIG. 1 shows a GLC trade of the crude product before fractionalredistillation (1/4"×10', 10% SE-30 packed column, 220° C., isothermal).

FIG. 2 shows the NMR spectrum of Fraction 6 of the redistillation.

FIG. 3 shows the CMR spectrum of Fraction 6.

FIG. 4 shows the IR spectrum of Fraction 6.

EXAMPLE II Preparation of1,3,4,6,7,8-Hexahydro-6-isopropyl-4,7,8,8-Tetramethylcyclopenta[G]-2-Benzopyranand1,3,4,6,7,8-hexahydro-8-Isopropyl-4,6,6,7-Tetramethylcyclopenta[G]-2-Benzopyran##STR40##

A stirred slurry of the indanethanol mixture (150 grams, as prepared inExample I), 20 grams of para-toluene-sulfonic acid, 65 grams ofisopropyl alcohol and 21 grams of paraformaldehyde is heated to 93° C.(reflux) for three hours. The mass is then heated to 150° C. withconcomitant distillation of lower boiling solvents. The reaction mass isaged three hours at 150° C., then cooled to 80° C. Toluene (100 mls) and200 mls of 5% sodium hydroxide solution are added thereto with stirring.The mass is cooled and the aqueous (lower) layer is separated anddiscarded. The organic layer is washed with water and distilled througha short column to afford 153 grams of crude product. This material isfractionally redistilled through a 4 foot vigreux column to affordpurified material. The mixture of1,3,4,6,7,8-hexahydro-6-isopropyl-1,7,8,8-tetramethyl[G]-2-benzopyranand1,3,4,6,7,8-hexahydro-6-isopropyl-1,7,8,8-tetramethylcyclopenta[G]-2-benzopyran(b.p. 135° C., 1.8 mm. Hg. pressure).

FIG. 5 is the GLC trace of the crude reaction product (1/4"×10', 10%SE-30 packed column, 220° C., isothermal).

FIG. 6 is the NMR spectrum of Fraction 7 of the distillation.

FIG. 7 is the IR spectrum of Fraction 7 of the distillation.

EXAMPLE III Preparation of 3-Isopropyl-β,1,1,2-Tetramethyl-5-IndanethylMethyl Ether and 1-Isopropyl-β,2,3,3-Tetramethyl-5-Indanethyl MethylEther ##STR41##

To a stirred slurry of 55% sodium hydride (18 grams) in 200 grams oftoluene is added dropwise a solution of 50 grams of the alcohol mixture(as prepared in Example I) in 100 grams of toluene at 10° C. The slurryis stirred for 30 minutes until hydrogen gas evolution ceases. Thetemperature of the reaction mass is adjusted to 40° C. and a solution of64 grams of methyl iodide in 50 grams of toluene is added dropwise in 30minutes. The reaction mass is stirred for 15 minutes and then cooled.Three hundred mls of water are carefully added. The organic layer isseparated and washed twice with water. Distillation through a shortcolumn affords 48 grams of crude product containing3-isopropyl-β,1,1,2-tetramethyl-5-indanethyl methyl ether and1-isopropyl-β,2,3,3-tetramethyl-5-indanethyl methyl ether.Redistillation through a 2' vigreux column with fractionation affordsthe product mixture in high purity (b.p. 125°-130° C. at 1.6 mm Hg.pressure).

FIG. 8 is the GLC trace of the crude reaction mass (1/4"×10', 10% SE-30packed column, 220° C., isothermal).

FIG. 9 shows the NMR spectrum of Fraction 5.

FIG. 10 shows the IR spectrum of Fraction 5.

EXAMPLE IV Preparation of 3-Isopropyl-1,1,2-Trimethyl-5-Indanethanol and1-Isopropyl-2,3,3-Trimethyl-5-Indanethanol ##STR42##

To a well-stirred mixture of 1,1,2-trimethyl-3-isopropylindane (1200grams), isooctane (500 grams), and aluminum chloride (407 grams) isadded over a three-hour period through a subsurface feed inlet, asolution of 840 grams of 1,1,2-trimethyl-3-isopropylindane, 340 grams ofisooctane and 132 grams of ethylene oxide. External cooling is used tokeep the temperature between -5° C. and 0° C. The reaction mass isstirred at -5° C. for 10 minutes, then poured quickly into 4 liters ofwell-stirred ice water. The reaction mass is stirred for 10 minutes thenallowed to settle into two clear layers. The aqueous (bottom) layer isdiscarded and the organic layer is washed twice with water, neutralizingwith sodium carbonate during the second wash.

The organic solution is distilled under vacuum to afford recoveredisooctane and 1,1,2-trimethyl-3-isopropylindane. Also, 173 grams of amixture of 3-isopropyl-1,1,2-trimethyl-5-indanethanol and1-isopropyl-2,3,3-trimethyl-5-indanethanol are collected. This materialis further purified by fractional distillation through a 1"×12" Goodloe®packed column (b.p. 143° C. to 146° C. at 0.7 mm Hg. pressure).

FIG. 11 shows a GLC trace of the crude reaction mass before distillation(1/4"×10', 10% SE-30 packed column, 220° C. isothermal).

FIG. 12 shows the NMR spectrum of Fraction 4.

FIG. 13 shows the IR spectrum of Fraction 4.

EXAMPLE V Preparation of1,3,4,6,7,8-Hexahydro-6-Isopropyl-7,8,8-Trimethylcyclopenta[G]-2-Benzopyranand1,3,4,6,7,8-Hexahydro-8-Isopropyl-6,7,7-Trimethylcyclopenta[G]-2-Benzopyra##STR43##

To a solution of 150 grams of the indanethanol (as prepared in ExampleIV) in 60 grams of isopropanol, is added 20 grams of para-toluenesulfonic acid and 25 grams of paraformaldehyde. The mixture is heated toreflux for 3 hours (90°-93° C.) with stirring. The temperature is thenraised to 150° C. by distilling off lower boiling materials. Thereaction mass is stirred at 150° C. for three hours, then cooled to 80°C. Toluene (100 mls) and 5% sodium hydroxide (200 mls) are added theretowith stirring. The mass is cooled and the aqueous (lower) layer isseparated and discarded. The organic layer is washed with water anddistilled through a short column to afford 137 grams of crude product.This material is fractionally distilled through a 2' vigreux column toafford a mixture of1,3,4,6,7,8-hexahydro-6-isopropyl-7,8,8-trimethylcyclopenta[G]-2-benzopyranand1,3,4,6,7,8-hexahydro-6-isopropyl-7,8,8-trimethylcyclopenta[G]-2-benzopyran.

FIG. 14 represents the GLC trace of the crude reaction mass.

FIG. 15 represents the NMR spectrum of Fraction 5 of the distillation.

FIG. 16 represents the IR spectrum of Fraction 5 of the distillation.

EXAMPLE VI

The following basic pear flavor formulation is prepared:

    ______________________________________                                        Ingredients             Parts by Weight                                       ______________________________________                                        Vanillin                2.0                                                   Hexyl Acetate           8.0                                                   Hexyl Isobutyrate       20.0                                                  Trans-2-hexenal (10% in propylene glycol)                                                             2.0                                                   n-Hexanal               0.5                                                   Apple Fusel Oil         10.0                                                  Linalyl Isobutyrate     0.5                                                   Hexyl-2-methylbutyrate  10.0                                                  Sauge Sclaree (10% in propylene glycol)                                                               0.5                                                   Coriander Oil           0.5                                                   Food grade ethyl alcohol (aqueous, 95%)                                                               146.0                                                 Propylene glycol        800.0                                                 ______________________________________                                    

To a portion of the above basic pear flavor formulation, 0.02% by weightof the mixture produced according to Example II containing compoundshaving the structures: ##STR44## is added. To another portion of thebasic pear formulation, nothing is added. Both flavor formulations arecompared at the rate of 50 ppm in water and evaluated by a bench panelof four experienced tasters. All the tasters of the bench panel statethat the flavor containing the mixture of compounds having thestructures: ##STR45## has a more natural riper pear character. This pearcharacter is enhanced and longer lasting as a result of the addition ofthe mixture of compounds having the structures: ##STR46## Therefore, theflavor formulation containing the compounds having the structures:##STR47## is preferred. When the individual compounds of the mixture areused in place of the mixture of compounds, the same result is attained.

EXAMPLE VII

Granular detergent compositions prepared according to United KingdomPatent Specification No. 1,501,498 having the following formulae areprepared by spray-drying the following mixtures as indicated in thecolumns headed VII A, VII B, VII C and VII D.

    __________________________________________________________________________                         COMPOSITION IN % BY WEIGHT                                                    Example                                                                            Example                                                                            Example                                                                            Example                                                                            Example                              Ingredient           VII A                                                                              VII B                                                                              VII C                                                                              VII D                                                                              VII E                                __________________________________________________________________________    Sodium salt of       14.1 14.1 14.1 14.1                                      ethoxylated fatty                                                             alcohol sulfate                                                               having an average                                                             of about 2.25 moles                                                           of ethylene oxide                                                             per mole of fatty                                                             alcohol                                                                       Sodium tallow alkyl  2.4  2.4  2.4  2.4                                       sulfate                                                                       Sodium silicate      0.0  2.0  6.0  6.0                                       solids ratio:                                                                 SiO.sub.2 /Na.sub.2 O = 2.0                                                   Sodium silicate      1.0  0.0  0.0  6.0                                       solids ratio:                                                                 SiO.sub.2 /Na.sub.2 O = 3.2                                                   Sodium tripolyphos-  24.0 24.0 24.0 24.0                                      phate                                                                         Na.sub.12 (AlO.sub.2 . SiO.sub.2).sub.12                                                           18.0 18.0 18.0 18.0                                      27H.sub.2 O                                                                   Moisture             10.0 10.1 9.9  10.2                                      Sodium sulfate       25.0 25.0 20.0 20.0                                      Minor ingredients    4.0  2.4  3.6  2.3                                       including sodium                                                              toluene sulfonate,                                                            trisodium sulfo-                                                              succinate, dyes, and                                                          brighteners                                                                   Mixtures of compounds produced according                                                           1.5  0.0  0.0  0.0  0.0                                  to Example I having the structures:                                            ##STR48##                                                                       +                                                                           ##STR49##                                                                    Mixture of compounds having the                                                                    0.0  2.0  0.0  0.0  0.0                                  structures:                                                                    ##STR50##                                                                      +                                                                            ##STR51##                                                                    produced according to Example II.                                             Mixture of compounds having the                                                                    0.0  0.0  2.0  0.0  0.0                                  structures:                                                                    ##STR52##                                                                      +                                                                            ##STR53##                                                                    produced according to Example III.                                            Mixture of compounds having the                                                                    0.0  0.0  0.0  3.0  0.0                                  structures:                                                                    ##STR54##                                                                      +                                                                            ##STR55##                                                                    produced according to Example IV.                                             Mixture of compounds having the                                                                    0.0  0.0  0.0  0.0  3.0                                  structures:                                                                    ##STR56##                                                                      +                                                                            ##STR57##                                                                    produced according to Example V.                                              __________________________________________________________________________

Laundry solutions containing the above detergent compositions are usedto launder fabrics. Each of the laundry compositions both prior to andon laundering gives rise to an intense sweet, musky aroma.

EXAMPLE VIII Perfumed Liquid Detergent

Concentrated liquid detergents with a sweet, musky aroma are preparedcontaining 0.10%, 0.15% and 0.20% of the mixture of compounds producedaccording to Example V having the structures: ##STR58## They areprepared by adding and homogeneously admixing the appropriate quantityof mixture of compounds having the structures: ##STR59## in the liquiddetergent. The liquid detergent is a builder-free liquid detergentconsisting of (a) 50% of a non-ionic surfactant having an HLB of 8.0 anda critical micelle concentration of 0.007, weight % of 25° C.; (b) anionic surfactant which is triethanolamine prepared according to UnitedKingdom Patent Specification No. 1,491,603.

The detergents all possess sweet, musky fragrances, the intensityincreasing with greater concentrations of mixtures of compounds havingthe structures: ##STR60##

EXAMPLE IX A. Powder Form

20 Grams of the flavor composition of Example VI which flavorcomposition contains a mixture of tricyclic isochromans having thestructures: ##STR61## is emulsified in a solution containing 300 gramsgum acacia and 700 grams water. The emulsion is spray-dried with a BowenLab Model Drier utilizing 250 c.f.m. of air with an inlet temperature of500° F., and outlet temperature of 200° F. and a wheel speed of 50,000r.p.m.

B. Paste Blend

The following mixture is then prepared:

    ______________________________________                                        Ingredients            Parts by Weight                                        ______________________________________                                        Liquid Flavor Composition of                                                                         48.4                                                   Example VI                                                                    Cab-o-Sil M-5           3.2                                                   (Brand of Silica produced by the Cabot                                        Corporation of 125 High Street, Boston,                                       Mass., 02110); Physical Properties:                                           Surface Area: 200m.sup.2 /gm                                                  Nominal Particle Size: 0.012 microns                                          Density: 2/3 lbs./cu.ft.                                                      ______________________________________                                    

The Cab-O-Sil is dispersed in the liquid flavor composition withvigorous stirring, thereby resulting in a viscous liquid. 48.4 Parts byweight of the powder flavor composition prepared in Part A is thenblended into the said viscous liquid, with stirring at 25° C. for aperiod of 30 minutes, resulting in a thixotropic sustained releaseflavor paste.

EXAMPLE X Chewing Gum

100 Parts by weight of chicle are mixed with 4 parts by weight of theflavor prepared in accordance with Example IX. 30 Parts of sucrose and100 parts of corn syrup are added. Mixing is effected in a ribbonblender with jacketed side walls of the type manufactured by the BakerPerkins Co.

The resultant chewing gum blend is then manufactured into strips 1 inchin width and 0.1 inches in thickness. The strips are cut into lengths of3 inches each. On chewing the chewing gum has a pleasant long-lastingpear flavor.

EXAMPLE XI Toothpaste Formulation

The following separate groups of ingredients are prepared:

    ______________________________________                                        Group "A"                                                                     30.200         Glycerin                                                       15.325         Distilled water                                                 .100          Sodium Benzoate                                                 .125          Saccharin Sodium                                                .400          Stannous Fluoride                                              Group "B"                                                                     12.500         Calcium Carbonate                                              37.200         Dicalcium Phosphate                                                           (Dihydrate)                                                    Group "C"                                                                      2.000         Sodium n-Lauroyl Sarcosinate                                                  (foaming agent)                                                Group "D"                                                                      1.200         Flavor Material of                                             100.00 (TOTAL) Example IX                                                 

PROCEDURE:

1. To ingredients in Group "A" are stirred and heated in a steamjacketed kettle to 160° F.

2. Stirring is continued for an additional three to five minutes to forma homogeneous gel.

3. The powders of Group "B" are added to the gel, while mixing until ahomogeneous paste is formed.

4. With stirring, the flavor of "D" is added and lastly the sodiumn-lauroyl sarcosinate.

5. The resultant slurry is then blended for one hour. The completedpaste is then transferred to a three roller mill and then homogenized,and finally tubed.

The resulting toothpaste when used in a normal toothbrushing procedureyields a pleasant pear flavor of constant strong intensity throughoutsaid procedure (1-1.5 minutes).

EXAMPLE XII Chewable Vitamin Tablets

The flavor material produced according to the process of Example IX isadded to a Chewable Vitamin Tablet Formulation at a rate of 5 gm/kgwhich Chewable Vitamin Tablet Formulation is prepared as follows:

    ______________________________________                                        Ingredients            Gms/Tablets                                            ______________________________________                                        Vitamin C (Ascorbic acid)                                                                            70.0                                                   as ascorbic acid-solution mixture 1:1                                         Vitamin B.sub.1 (thiamine mononitrate)                                                               4.0                                                    as Rocoat® thiamine mononitrate 33%                                       (Hoffman La Roche)                                                            Vitamin B.sub.2 (riboflavin)                                                                         5.0                                                    as Rocoat® riboflavin 331/3%                                              Vitamin B.sub.6 (pyridoxine hydrochloride)                                                           4.0                                                    as Rocoat® pyridoxide hydrochloride                                       331/3%                                                                        Niacinamide            33.0                                                   as Rocoat® niacinamide 331/3%                                             Calcium pantothenate   11.5                                                   Vitamin B.sub.12 (cyanocobalamin)                                                                    3.5                                                    as Merck 0.1% in gelatin                                                      Vitamin E (dl-alpha tocopheryl acetate                                                               6.6                                                    as dry Vitamin E acetate 331/3% Roche                                         d-Biotin               0.044                                                  Certified lake color   5.0                                                    Flavor of Example IX   5.0                                                    Sweetener-sodium saccharin                                                                           1.0                                                    Magnesium stearate lubricant                                                                         10.0                                                   Mannitol q.s. to make  500.0                                                  ______________________________________                                    

Preliminary tablets are prepared by slugging, with flatfaced punches andgrinding the slugs to 14 mesh. 13.5 g dry Vitamin A Acetate and 0.6 gVitamin D are then added as beadlets. The entire blend is thencompressed using concave punches at 0.5 g each.

Chewing of the resultant tablet yields a pleasant, long-lsting,consistently strong pear flavor for a period of 12 minutes.

EXAMPLE XIII Musk Perfume Formulation

The following musk perfume formulation is prepared:

    ______________________________________                                        Ingredients          Parts by Weight                                          ______________________________________                                        Musk Ambrette        200                                                      Musk Ketone          200                                                      Beta Ionone          50                                                       Vetiveryl Acetate    50                                                       Sandlwood Oil        100                                                      Benzoyl Benzoate     400                                                      Mixture of tricyclic isochromans                                                                   20                                                       prepared according to Example II                                              ______________________________________                                    

The mixture of tricyclic isochromans of Example II imparts to this muskformulation, a natural, sweet, musk aroma with great intensity.

EXAMPLE XIV Preparation of a Soap Composition

100 Grams of soap chips are mixed with 1 gram of the perfume compositionof Example XIII until a substantially homogeneous composition isobtained. The perfumed soap compositon manifests an excellentanimal-musk, sweet, musk aroma.

EXAMPLE XV Preparation of a Soap Composition

100 Grams of soap chips are mixed with 1 gram of the indane alkanemixture produced according to Example I until a substantiallyhomogeneous composition is obtained. The perfumed soap compositionmanifests an excellent musk aroma.

EXAMPLE XV Preparation of a Cologne and Handkerchief Perfume

The mixture of indane alkanol methyl ethers having the structures:##STR62## prepared according to Example III is incorporated into acologne at concentrations of 1.5%, 2.0%, 2.5%, 3.0%, 3.5% and 4.0% in85% aqueous ethanol; and into handkerchief perfumes at concentrations of15%, 20%, 25% and 30% (in 95% aqueous ethanol). Distinct and definitesweet, musk fragrances are produced and imparted to the cologne and tothe hankerchief perfume at each of the levels indicated.

EXAMPLE XVI Preparation of a Cosmetic Powder Composition

A cosmetic powder is prepared by mixing in a ball mill, 100 grams oftalcum powder with 0.15 grams of the mixture of indane alkanol methylethers produced according to Example III. The resulting powder has anexcellent sweet, musk aroma.

EXAMPLE XVII

Utilizing the procedure of Example I of column 15 of U.S. Pat. No.3,632,396, a nonwoven cloth substrate useful as a dryer-addedfabric-softening article of manufacture is prepared wherein thesubstrate, the substrate coating and the outer coating and the perfumingmaterial are as follows:

    ______________________________________                                        1.        a water "dissolvable" paper ("Dissolvo                                        Paper");                                                            2.        Adogen 448 (m.p. about 140° F.) as the                                 substrate coating; and                                              3.        an outer coating having the following                                         formulation (m.p. about 150° F.):                                     57 percent C.sub.20-22 HAPS                                                   22 percent isopropyl alcohol                                                  20 percent antistatic agent                                                    1 percent of the mixture of indane                                            alkanols prepared according to Example                                        IV having the structures:                                                     ##STR63##                                                                      +                                                                            ##STR64##                                                           ______________________________________                                    

Fabric-softening compositions prepared as set forth above having anaroma characteristic which can be described as sweet and muskyessentially consist of a substrate having a weight of about 3 grams per100 square inches, a substrate coating of about 1.85 grams per 100square inches of substrate and an outer coating of about 1.4 grams per100 square inches of substrate thereby providing a total aromatizedsubstrate and an outer coating weight ratio of about 1:1 by weight ofthe substrate. A sweet, musky aroma is imparted in a pleasant manner tothe head space in the dryer on operation thereof using the said dryeradded fabric softening nonwoven fabric. When the individual componentsof the mixture are used in place of the mixture, that is, the componentshaving the structure: ##STR65## are used, a substantially identicalresult is achieved.

EXAMPLE XVIII

Utilizing the procedure of Example I of column 15 of U.S. Pat. No.3,632,396, a nonwoven cloth substrate useful as a dryer-addedfabric-softening article of manufacture is prepared wherein thesubstrate, the substrate coating and outer coating and the perfumingmaterial are as follows:

    ______________________________________                                        1.        a water "dissolvable" paper ("Dissolvo                                        Paper");                                                            2.        Adogen 448 (m.p. about 140° F.) as the                                 substrate coating; and                                              3.        an outer coating having the following                                         formulation (m.p. about 150° F.):                                     57 Percent C.sub.20-22 HAPS                                                   22 percent isopropyl alcohol                                                  20 percent antistatic agent                                                    1.5 percent of the compound having the                                        structure:                                                                    ##STR66##                                                                    prepared according to Example II.                                    ______________________________________                                    

A fabric-softening composition prepared as set forth above having anaroma characteristic which can be described as sweet and muskyessentially consists of a substrate having a weight of about 3 grams per100 square inches, a substrate coating of about 1.85 grams per 100square inches of substrate and an outer coating of about 1.4 grams per100 square inches of substrate, thereby providing a total aromatizedsubstrate and an outer coating weight ratio of about 1:1 by weight ofthe substrate. The resulting aroma is described as sweet and musky andis imparted in a pleasant manner to the head space in the dryer onoperation thereof using the said dryer added fabric softening nonwovenfabric.

EXAMPLE XIX Preparation of a Soap Composition

100 Grams of soap chips are prepared according to Example V of U.S. Pat.No. 4,058,490, issued on Nov. 15, 1977 as follows:

"The sodium salt of an equal mixture of C₁₀ /C₁₄ alkane sulfonates (95%active), 40 lbs. is dissolved in a mixture of 80 lbs. of anhydrousisopropanol and 125 lbs. of deionized water at 150° F. In this mixtureis dissolved 10 lbs. of partially hydrogenated coconut oil fatty acidsand 15 lbs. of sodium mono-C₁₄ -alkyl maleate, and the pH of thissolution is adjusted to 6.0 by the addition of a small amount of a 50%aqueous solution of NaOH. The isopropanol is distilled off and theremaining aqueous solution is dried. The resulting solid actives arethen blended in a chip mixer with 10 lbs. water, 0.2 lb. titaniumhydroxide"

The resulting blend is then mixed with 1 gm of the compound having thestructure: ##STR67## prepared according to Example V until asubstantially homogeneous composition is obtained. The perfumed soapcomposition manifests an excellent sweet, musk aroma.

EXAMPLE XX Preparation of a Soap Composition

100 Grams of soap chips are prepared according to Example V of U.S. Pat.4,058,490, issued on Nov. 15, 1977 as follows:

"The sodium salt of an equal mixture of C₁₀ /C₁₄ alkane sulfonates (95%active), 40 lbs. is dissolved in a mixture of 80 lbs. of anhydrousisopropanol and 125 lbs. of deionized water at 150° F. In this mixtureis dissolved 10 lbs. of partially hydrogenated coconut oil fatty acidsand 15 lbs. of sodium mono-C₁₄ -alkyl maleate, and the pH of thissolution is adjusted to 6.0 by the addition of a small amount of a 50%aqueous solution of NaOH. The isopropanol is distilled off and theremaining aqueous solution is dried. The resulting solid actives arethen blended in a chip mixer with 10 lbs. water, 0.2 lb. titaniumhydroxide"

The resulting blend is then mixed with 1 gm of the compound havingthestructure: ##STR68## prepared according to Example I until asubstantially homogeneous composition is obtained. The perfumed soapcomposition manifests an excellent sweet, musk aroma.

What is claimed is:
 1. A mixture of compounds having the structures:##STR69##